Synthesis and Evaluation of Antibacterial Activity of Cyclopropylphosphonates

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅或者付费存取

详细

Phosphonyl-substituted cyclopropanes were obtained by the reaction of O,O-diethyl (1,2-dibromoethyl)phosphonate with CH-acids, in particular, acetylacetone, acetoacetic and malonic esters, ethyl ester and amide of cyanoacetic acid, and benzyl cyanide, in the presence of a base in acetonitrile at room temperature. Antibacterial activity of the starting phosphonate and its derivatives was studied.

作者简介

G. Gasparyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia

A. Bichakhchyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia

L. Derdzyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia

T. Khachatryan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia

L. Gasparyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia

Z. Mardiyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia; SPC «Armbiotechnology» of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0056 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia; Yerevan, 0056 Armenia

R. Muradyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia

H. Arakelyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia

Email: arpenikb@mail.ru
Yerevan, 0014 Armenia

A. Poghosyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0014 Armenia; SPC «Armbiotechnology» of the National Academy of Sciences of the Republic of Armenia, Yerevan, 0056 Armenia

编辑信件的主要联系方式.
Email: arpenikb@mail.ru
Yerevan, 0014 Armenia; Yerevan, 0056 Armenia

参考

  1. Shneider T.F., Kaschel J., Werz D.B. // Angew. Chem. Int. Ed. 2014. Vol. 53. P. 5504. doi: 10.1002/anie.201309886.3
  2. Ding Z., Liu Z., Wang Z., Yu T., Xu M., Wen J., Yang K., Zhang H., Xu L., Pengfei L. // J. Am. Chem. Soc. 2022. Vol. 144. P. 8870. doi: 10.1021/jacs.2c03673
  3. Verma K., Banerjee P. // Adv. Synth. Catal. 2017. Vol. 359. P. 3848. doi: 10.1002/adsc.201700744
  4. Parsons A.T., Johnson J.S. // J. Am. Chem. Soc. 2009. Vol. 131. P. 3122. doi: 10.1021/ja809873u
  5. Kreft A., Jones P.G., Wers D.B. // Org. Lett. 2018. Vol. 20. P. 2059. doi: 10.1021/acs.orglett.8b00603
  6. Liu H., Tian L., Wang H., Li Z.-Q., Zhang C., Xue F., Feng C. // Chem. Sci. 2022. Vol. 13. P. 2686. doi: 10.1039/D2SC00302C
  7. Yang G., Sun Y., Shen Y., Chai Z., Zhou S., Chu J., Chai J. // J. Org. Chem. 2013. Vol. 78. P. 5393. doi: 10.1021/jo400554a
  8. Chu Z.-Y., Li N., Liang D., Li Z.-H., Zheng Y.-S., Liu J.-K. // Tetrahedron Lett. 2018. Vol. 59. P. 715. doi: 10.1016/j.tetlet.2018.01.016
  9. Parson A.T., Smith A.G., Neel A.J., Johnson J.S. //J. Am. Chem. Soc. 2010. Vol. 132. P. 9688. doi: 10.1021/ja1032277
  10. Garve L.K.B., Kreft A., Jones P.G., Werz D.B. // J. Org. Chem. 2017. Vol. 82. P. 9235. doi: 10.1021/acs.joc.7b01631
  11. Ming B., Doyle M.P. // Org. Lett. 2023. Vol. 25. P. 3029. doi: 10.1021/acs.orglett.3c00831
  12. Sapeta K., Kerr M.A. // J. Org. Chem. 2007. Vol. 72. P. 8597. doi: 10.1021/jo701606u
  13. Goldberg A.F.G., O’Connor N.R., Craig II R.A., Stoltz B.M. // Org. Lett. 2012. Vol. 14. P. 5314. doi: 10.1021/ol302494n
  14. Augustin A.U., Sensse M., Jones P.G., Werz D.B. // Angew. Chem. Int. Ed. 2017. Vol. 56. P. 14293. doi: 10.1002/anie.201708346
  15. Augustin A.U., Busse M., Jones P.G., Werz D.B. // J. Org. Lett. 2018. Vol. 20. P. 820. doi: 10.1021/acs.orglett.7b03961
  16. Xie M.S., Zhao G.-F., Qin T., Suo Y.-B., Qu G.-R., Guo H.-M. // Chem. Commun. 2019. Vol. 55. P. 1580. doi: 10.1039/c8cc09595g
  17. Wang S., Xie Z., Li M., Wang C. // ChemistrySelect. 2020. Vol. 5. P. 6011. doi: 10.1002/slct.202000810
  18. Cavitt M.A., Phun L.H., France S. // Chem. Soc. Rev. 2014. Vol. 43. P. 804. doi: 10.1039/c3cs60238a
  19. Deepthi A., Meenakshy C.B., Maneesh M. // Synthesis. 2023. Vol. 55. P. 3875. doi: 10.1055/a-2096-4302
  20. De Clercq E. // Pure Appl. Chem. 1998. Vol. 70. P. 567. doi: 10.1351/pac19980030567
  21. Pyun H.J., Clarke M.O., Cho A., Casarez A., Ji M., Fardis M., Pastor R., Sheng X.C., Kim C.U. // Tetrahedron Lett. 2012. Vol. 53. P. 2360. doi: 10.1016/J.tetlet.2012.02.111
  22. Midura W.H., Krysiak J.A., Rzewnicka A., Lyzwa P., Ewas A.M. // Tetrahedron. 2013. Vol. 69. P. 730. doi: 10.1016/j.tet.2012.10.085
  23. Devreux V., Wiesner J., Goeman J.L., Eycken J.V., Jomaa H., Calenbergh S.V. // J. Med. Chem. 2006. Vol. 49. P. 2656. doi: 10.1021/jm051177c
  24. Lewis R.T., Motherwell W.B. // Tetrahedron Lett. 1998. Vol. 29. P. 5033. doi: 10.1016/S0040-4039(00)80672-3
  25. Chanthamath S., Ozaki S., Shibatomi K., Iwasa S. // J. Org. Lett. 2014. Vol. 16. P. 3012. doi: 10.1021/ol501135p
  26. Midura W.H., Krysiak J.A., Mikolajczyk M. // Tetrahedron Asym. 2003. Vol. 14. P. 1245. doi: 10.1016/S0957-4166(03)00211-8
  27. Midura W.H., Sobczak A., Paluch P. // Tetrahedron Lett. 2013. Vol. 54. P. 223. doi: 10.1016/j.tetlet.2012.11.002
  28. Midura W.H., Rzewnicka A., Krysiak J.A. // Phosphorus, Sulfur, Silicon, Relat. Elem. 2017. Vol. 192. P. 180. doi: 10.1080/10426507.2016.1250763
  29. Hirao T., Hagihara M., Ohshiro Y., Agawa T. // Synthesis. 1984. Vol. 1984. P. 60. doi: 10.1055/S-1984-30731
  30. Gasparyan G.Ts., Bichakhchyan A.S., Derdzyan L.V., Avetisyan S.Kh., Panosyan H.A., Poghosyan A.S. // Russ. J. Gen. Chem. 2024. Vol. 94. P. 62. doi: 10.1134/S1070363224010055
  31. Гаспарян Г.Ц., Овакимян М.Ж., Погосян А.С., Бичахчян А.С., Дердзян Л.В., Паносян Г.А. // ЖОрХ. 2022. T. 58. C. 1393; Gasparyan G.Ts., Оvakimyan M.Zh., Poghosyan A.S., Bichakhchyan A.S., Derdzyan L.V., Panosyan H.A. // Russ. J. Org. Chem. 2022. Vol. 58. P. 1989. doi: 10.1134/S1070428022120314
  32. Кормачев В.В., Федосеев М.С. Препаративная химия фосфора, Пермь: Уральское отделение РАН, Институт технической химии, 1992. С. 184.
  33. Weglarz-Tomczak E., Staszewska K., Talma M., Mucha A. // Tetrahedron Lett. 2016. Vol. 57. P. 4812. doi: 10.1016/j.tetlet.2016.09.051
  34. Руководство по проведению доклинических исследований лекарственных средств / Под ред. А.Н. Миронова. М.: Медицина, 2012. C. 509.

补充文件

附件文件
动作
1. JATS XML
下载

版权所有 © Russian Academy of Sciences, 2025